Midi Holiday Dresses

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Chic Midi Holiday Dresses for a Perfect Holiday Look

Find your perfect balance with Windsor's midi holiday dresses, an ideal choice for versatile, chic holiday party looks. These dresses offer a flattering length for any occasion, from family gatherings to formal dinners. Choose satin midis for a polished look that pairs effortlessly with heels or opt for velvet or lace for a bit of extra texture. Colors like classic red, green, and even black capture the holiday spirit, while details like side slits and subtle embellishments bring sophistication. Whether you’re dressing for day or night, a midi holiday dress will have you turning heads this season.

  • Refined Chic Ribbed Midi Dress

    Simple, sleek, and seriously versatile. This ribbed midi dress nails that effortlessly polished vibe with a body-hugging fit and mock neckline. Style with gold hoops and slides for brunch—or heels and a blazer for a polished look for a business lunch.

    Fit & Features

    • Soft rib knit stretch fabric, knit lining
    • Sleeveless mock neckline
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000337

    Category Name: Midi Holiday Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, L

  • Kaylee Velvet Strapless Midi Formal Dress

    Special Occasion

    Sleek, sculpted, and ready to turn heads—The Kaley formal dress brings effortless allure to every RSVP. Cut from plush velvet, this strapless bodycon midi hugs your curves with a ruched front seam and flirty slit that was made for a slow-motion entrance.

    Fit & Features

    • Luxe velvet knit fabric lined with stretchy knit
    • Strapless neckline, padded bra cups
    • Back zipper and hook-eye closure
    • Front ruched seam and slit
    • Bodycon fit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, cocktail parties, formal celebrations, fancy date nights, birthdays, engagement parties, rehearsal dinners, upscale social events, art gallery openings

    Style Number/Barcode: 05001-000466

    Category Name: Midi Holiday Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: HUNTER, NAVY, PURPLE

    Available Size: XS, S, M, L, XL

  • Krystal Satin Midi Formal Dress

    Special Occasion

    Designed for the kind of night that deserves a slow entrance, the Krystal satin midi dress molds to your shape with a strapless neckline, hip-pleated seams, and a daring front slit. It’s sleek, sculpted, and made to turn every glance into a double take.

    Fit & Features

    • Stretch satin-lined fabric
    • Strapless neckline, padded bra cups
    • Back zipper and hook-eye closure
    • Front slit
    • Form-hugging fit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, rehearsal dinners, engagement parties, formal celebrations, birthdays, date nights, cocktail parties, holiday soirees

    Style Number/Barcode: 05001-000559

    Category Name: Midi Holiday Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: HUNTER

    Available Size: XS, S, M, L, XL

  • Darcy Velvet Bow Midi Formal Dress

    Special Occasion

    Romantic with a refined edge, the Darcy velvet midi dress blends timeless polish with a touch of drama. Framed by soft cap sleeves and a classic crew neckline, the open back tied in a bow makes every exit just as striking as the entrance.

    Fit & Features

    • Soft velvet fabric, stretchy knit lining
    • Crew neckline
    • Cap sleeves
    • Open back with bow, lower center back slit
    • Form-hugging silhouette
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, cocktail parties, formal celebrations, date nights, rehearsal dinners, engagement parties, holidays

    Style Number/Barcode: 05001-000524

    Category Name: Midi Holiday Dresses

    Price: $59.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Shimmer Agenda Glitter Midi Dress

    Made to shine under every light. This glitter knit midi dress features a sweetheart neckline, ruched seams, and a curve-hugging fit that’s equal parts sultry and sophisticated.

    Fit & Features

    • Glitter knit fabric, sewn-in knit lining, moderate stretch
    • Sweetheart neckline, padded bra cups
    • Adjustable spaghetti straps
    • Ruched bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000234

    Category Name: Midi Holiday Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L, XL

  • Effortless Grace Chiffon Midi Dress

    The dress that never tries too hard—but always delivers. This chiffon halter midi flows with every step, featuring a plunging neckline, open back, and A-line skirt that moves effortlessly from the reception to the dance floor.

    Fit & Features

    • Airy chiffon-lined fabric
    • Halter V-neckline, tie closure, back zipper and hook-eye closure
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000644

    Category Name: Midi Holiday Dresses

    Price: $56.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Velvet Dream One Shoulder Midi Dress

    Elegance with a little edge. This one-shoulder velvet midi dress features a soft curve-hugging fit, knotted trim detail, and a subtle trumpet hem that moves beautifully with every step—made for holiday soirées and cocktail nights alike.

    Fit & Features

    • Soft velvet-lined fabric
    • One-shoulder neckline with knotted accent
    • Curve-hugging silhouette
    • Trumpet flared midi-length hem 
    • Runs true to size

    Style Number/Barcode: 05101-000772

    Category Name: Midi Holiday Dresses

    Price: $19.97 $40.90

    On Sale: Yes

    Availability: In Stock

    Available Color: HUNTER

    Available Size: XS, S, M, L, XL

    Product Badge:
    • Sale
  • Camilla Satin Cutout Slit Midi Formal Dress

    Special Occasion

    Designed to catch the light—and their attention—the Camilla formal dress pairs a lustrous satin finish with a sultry waist cutout and draped cowl neckline. The midi silhouette and thigh-high slit strike the perfect balance between effortless allure and timeless polish.

    Fit & Features

    • Stretch satin fabric
    • Cowl neckline
    • Adjustable spaghetti straps
    • Cutout bodice, front slit
    • Form-hugging silhouette
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Cocktail parties, weddings, date nights, birthdays, holiday celebrations, fashion events, art gallery openings, formal brunches, rehearsal dinners, luxury lounges

    Style Number/Barcode: 05001-000450

    Category Name: Midi Holiday Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, XL

  • Twist the Plot Bodycon Midi Dress

    A little sheer, a little sculpted—this mesh off-shoulder midi is your new statement staple. With its asymmetrical neckline and ruched detailing, it hugs every curve while keeping things effortlessly elevated.

    Fit & Features

    • Mesh fabric lined with stretch knit
    • Asymmetrical off-the-shoulder neckline
    • Ruched side seams
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000410

    Category Name: Midi Holiday Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M

  • Twist Of Noir Velvet Midi Dress

    Classic with a sultry twist. This flocked velvet strapless midi features a ruched sweetheart neckline and front slit for an elegant yet daring finish that’s made to turn heads.

    Fit & Features

    • Flocked velvet fabric with stretch
    • Strapless neckline with twisted bust detail
    • Bodycon silhouette
    • Front slit accent
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000716

    Category Name: Midi Holiday Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XXS, XS, S

  • Glow With It Rhinestone Mesh Midi Dress

    Delicate, dreamy, and just the right amount of shimmer. This rhinestone mesh midi hugs your curves with ruched detailing and a sleek square neckline, catching the light (and attention) from every angle—perfect for cocktail nights, birthdays, or that glam “no special reason” moment.

    Fit & Features

    • Rhinestone-embellishments, mesh-lined fabric, moderate stretch
    • Square neckline
    • Adjustable spaghetti straps
    • Ruched bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000004

    Category Name: Midi Holiday Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Emme Flocked Velvet Midi Formal Dress

    Special Occasion

    Soft florals meet sculpted elegance in the Emme flocked mesh midi dress, designed with a square neckline and wide tank straps for a clean, modern feel. The side slit adds just the right amount of drama, while the pleated detailing shapes everything beautifully.

    Fit & Features

    • Flocked mesh fabric, lined
    • Square neckline with adjustable tank straps, padded bra cups
    • Back zipper and hook-eye closure
    • Side slit detail
    • Pleated bodycon silhouette
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, gala dinners, formal celebrations, holiday parties, cocktail soirees, birthdays, anniversaries

    Style Number/Barcode: 05001-000575

    Category Name: Midi Holiday Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: HUNTER

    Available Size: XS

    Product Badge:
    • Best Seller
  • Brenda Velvet Cutout Midi Formal Dress

    Special Occasion

    Designed for those slow-motion, all-eyes-up moments, the Brenda formal dress glows in luxe velvet with a sculpted bodycon fit that traces every curve. The cowl sweetheart neckline, front slit, and cutout twist back create an effortlessly refined silhouette that delivers chic drama from every angle.

    Fit & Features

    • Soft stretch velvet fabric lined with knit
    • Cowl neckline with tank-style straps, padded bra cups
    • Back cutout detail at the back with twist-knot design
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Front slit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, galas, formal celebrations, holiday parties, New Year's Eve, cocktail soirees, birthday dinners, fashion-forward events, art gallery openings, formal receptions, red-carpet occasions

    Style Number/Barcode: 05001-000585

    Category Name: Midi Holiday Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: HUNTER, NAVY

    Available Size: XS, S, M, L, XL

  • Crushworthy Mesh Ruched Midi Dress

    Made for evenings that call for a little drama, this mesh midi dress blends a soft cowl neckline with a delicate back slit for just the right dose of romance. The ruched fit sculpts beautifully, while the midi length keeps it sleek and elevated.

    Fit & Features

    • Mesh overlay fabric with smooth knit lining
    • Cowl neckline, lace padded bra cups
    • Adjustable spaghetti straps
    • Ruching throughout the bodice
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Back slit at hem, midi-length
    • Runs true to size

    Style Number/Barcode: 05101-000591

    Category Name: Midi Holiday Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L, XL

  • Sweetheart Chic Ruffle Midi Dress

    Romance with a little drama. This burnout velvet floral midi dress stuns with its cowl sweetheart neckline, body-hugging fit, and ruffled slit—perfect for weddings, date nights, or any luxe occasion.

    Fit & Features

    • Burnout velvet floral pattern, mesh-lined fabric
    • Sweetheart cowl neckline, padded bra cups
    • Adjustable spaghetti straps
    • Ruffled trim front slit
    • Bodycon fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000419

    Category Name: Midi Holiday Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, L, XL

    Product Badge:
    • Best Seller
  • Glam Obsessed Glitter Off-The-Shoulder Midi Dress

    This is the dress you reach for when you want the room to feel a tiny bit obsessed. The glitter knit hugs just right, the off-the-shoulder neckline adds that soft-but-sultry vibe, and the midi length keeps it effortlessly elevated.

    Fit & Features

    • Glitter knit fabric with moderate stretch, sewn-in knit lining
    • Sweetheart neckline with off-the-shoulder sleeves
    • Padded bra cups for support and shaping
    • All-over ruched detailing defines the figure
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000543

    Category Name: Midi Holiday Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: HUNTER

    Available Size: XS, S, M, L, XL

  • Valery Faux Leather Corset Midi Dress

    Special Occasion

    Made for the kind of entrance that turns heads without trying, the Valery faux leather corset midi dress brings a sleek, sculpted allure. The structured bodice, curve-skimming silhouette, and thigh-high slit work together to deliver that sultry, eyes-follow-you energy.

    Fit & Features

    • Coated faux leather fabric with a glossy finish, knit lining
    • Strapless neckline with structured seaming
    • Corset-inspired bodice paneling, flexible boning
    • Back zipper with hook-eye closure
    • Front slit adds movement
    • Midi-length bodycon silhouette
    • Runs true to size

     

    Where to Wear:

    Rooftop hotel bars, dressed-up dinner, formal date night, birthday celebration, and nights in the city.

    Style Number/Barcode: 05001-000596

    Category Name: Midi Holiday Dresses

    Price: $69.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L, XL

  • Laylin Velvet Lace-Up Midi Formal Dress

    Special Occasion

    Designed for evenings that call for confidence and quiet drama, the Laylin velvet bodycon midi dress moves with intention and allure. A square neckline, wrap front slit, and lace-up open back create a silhouette that feels sculpted, modern, and unmistakably polished.

    Fit & Features

    • Velvet-lined fabric with soft stretch
    • Square neckline with wide tank straps
    • Ruched wrap-style skirt with front slit
    • Midi-length silhouette
    • Lace-up back detail
    • Runs true to size

     

    Where to Wear:

    Weddings, formal holiday parties, rehearsal dinners, evening cocktail receptions, romantic dates, engagement parties, birthdays, cultural events, fancy occasions

    Style Number/Barcode: 05001-000597

    Category Name: Midi Holiday Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S

  • Plans After Sunset Midi Dress

    This is the kind of dress that doesn’t need an intro. Sleek, sculpted, and subtly shimmering, it moves with intention and lands every eye in the room.

    Fit & Features

    • Rhinestone floral detailing, mesh-lined fabric
    • V-neckline with halter spaghetti straps
    • Fitted bodice with seam shaping
    • Midi-length skirt with bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000626

    Category Name: Midi Holiday Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L, XL